A white church with a steeple and red accents, surrounded by autumn trees.

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Our top choices for Windham bed & breakfast

1. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (146 reviews)
"Breakfast was wonderful!"
United States
Karen
$238 nightly
The price is $260
Sep 10 - Sep 11
Total with taxes and fees
Fleetwood House Bed & Breakfast

2. Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.6 out of 10, Excellent, (1,130 reviews)
"Great place to stay, affordable,clean with walking access to to port area!"
United States
Steve Robert
$127 nightly
The price is $138
Sep 10 - Sep 11
Total with taxes and fees
Inn at St John Portland In-Town

3. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (97 reviews)
"It was wonderful staying. Beautiful old house with all amenities and"
United States
Svetlana
$257 nightly
The price is $280
Sep 21 - Sep 22
Total with taxes and fees
West End Collection at 146 Pine

4. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (129 reviews)
"Beautiful place to stay in the middle of a quiet street and walking distance to many spots. The rooms and common areas were clean and beautifully maintained. Staff was ready to answer any questions you had via phone or text. I loved this inn and would choose it again. Definitely recommend it !"
United States
Adriana Cecilia
$329 nightly
The price is $358
Sep 28 - Sep 29
Total with taxes and fees
Blind Tiger Portland – Carleton Street

5. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (179 reviews)
"Amazing stay in a perfect location! Would absolutely recommend to family and friends and will likely stay again!"
United States
Megan
$226 nightly
The price is $246
Sep 13 - Sep 14
Total with taxes and fees
The Orchard House: Inn & Cafe

6. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (487 reviews)
"Great location, quiet room, great breakfast......"
United States
Keith
$194 nightly
The price is $211
Sep 10 - Sep 11
Total with taxes and fees
Candlebay Inn

7. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (192 reviews)
"Enjoyable"
Canada
Lawrence
$332 nightly
The price is $362
Sep 27 - Sep 28
Total with taxes and fees
Blind Tiger Portland - Danforth Street.

8. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (1 review)
"The owners were amazing and so kind. The location is perfect, and the amenities feel so hoy and great."
United States
Meaghan
$305 nightly
The price is $332
Sep 10 - Sep 11
Total with taxes and fees
The Nicholson Inn

9. The Jeremiah Mason House B & B

The Jeremiah Mason House B & B
3.0 star property
Limerick
9.6 out of 10, Exceptional, (56 reviews)
"Absolutely amazing host and yummy breakfast!!"
United States
andy
$159 nightly
The price is $173
Sep 10 - Sep 11
Total with taxes and fees
The Jeremiah Mason House B & B

10. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (159 reviews)
"The room was lovely and comfortable, including easy-to-adjust air conditioning. Breakfast was delicious as were the homemade cookies available each evening. Coffee and tea were available all the time."
United States
Kenneth and
$232 nightly
The price is $253
Sep 13 - Sep 14
Total with taxes and fees
The Kendall Inn

11. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (192 reviews)
"Sean was amazingly helpful and friendly. The house itself is so well maintained, and the blue room was adorable. Loved the fact that we were within walking distance of all the shops. Would definitely recommend and will plan on staying again the next time we’re in town."
United States
Kim
$228 nightly
The price is $249
Sep 13 - Sep 14
Total with taxes and fees
The James Place Inn B&B

12. The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (127 reviews)
"Very nice accommodation"
United States
Shelly
$160 nightly
The price is $174
Sep 28 - Sep 29
Total with taxes and fees
The Perkins House

13. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very Good, (1,000 reviews)
"Beautiful property a short walk from the beach and all the attractions make it an ideal place to stay"
United States
James
$139 nightly
The price is $152
Sep 13 - Sep 14
Total with taxes and fees
Old Orchard Beach Inn

14. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
$264 nightly
The price is $288
Sep 20 - Sep 21
Total with taxes and fees
Experience the History of Portland - The Hope Island Room

15. Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.6 out of 10, Exceptional, (127 reviews)
"Comfortable, lovely view of garden, clean."
United States
Virginia
$162 nightly
The price is $176
Sep 13 - Sep 14
Total with taxes and fees
Noble House Inn

16. Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach

Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Definitely worth a visit! Beach just down the road!"
United States
Matt S.
$179 nightly
The price is $196
Sep 18 - Sep 19
Total with taxes and fees
Charming Top-Floor Queen Room with Sloped Ceilings, Walk to the Beach

17. The Munroe Inn

The Munroe Inn
3.5 star property
Auburn
9.2 out of 10, Wonderful, (76 reviews)
"Wonderful place to stay. The rooms are so comfortable and the host was very accommodating. Breakfast was outstanding and the best cup of coffee in Auburn. Such a gem of a place!"
United States
Tristan
$178 nightly
The price is $194
Sep 14 - Sep 15
Total with taxes and fees
The Munroe Inn

18. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
$356 nightly
The price is $388
Sep 21 - Sep 22
Total with taxes and fees
The Diamond Island Suite - Suite in Historic Home

19. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
$391 nightly
The price is $426
Sep 20 - Sep 21
Total with taxes and fees
Experience the History of Portland - The Hope Island Room

20. Experience the History of Portland - Two Room Suite w/Private Bath

Experience the History of Portland - Two Room Suite w/Private Bath
West End
$452 nightly
The price is $493
Sep 27 - Sep 28
Total with taxes and fees
Experience the History of Portland - Two Room Suite w/Private Bath
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham Hotel Reviews

Find out more about Windham

Windham B&B information

Number of reviews
3,608
Accommodation
35 B&B
Lowest Price
$138
Highest Price
$493

Frequently asked questions

What is the nightly rate for a B&B in Windham?
Prices for B&Bs in Windham often vary, but you can find a great deal from $138 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windham B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Windham?
The best time to book a B&B in Windham is during the vibrant fall season, particularly from September to October. This period is favored by travelers seeking a picturesque escape amid the stunning autumn foliage. As the leaves change, Windham transforms into a canvas of brilliant reds, oranges, and yellows, providing a breathtaking backdrop for outdoor activities and leisurely strolls.

September offers mild temperatures, typically ranging from the low 50s to mid-70s Fahrenheit, making it ideal for hiking and exploring the scenic trails in the Catskill Mountains. The comfortable climate invites visitors to engage in outdoor adventures, whether it's a hike to the summit of Windham Mountain or a bike ride through the charming countryside.

If you are considering a more budget-friendly option, late October can be particularly appealing. This month often features fewer crowds, allowing for a peaceful retreat where you can enjoy the lingering fall beauty without the hustle and bustle. Plus, many local businesses offer seasonal promotions, giving you the opportunity to enjoy quality experiences at a great value.
What is the difference between a Windham Bed & Breakfast and a hotel?
Every Windham B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windham B&Bs.

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